Skip to content

Better Decisions, Fewer Regrets Part 4 | "The Maturity Question"

Our natural inclination is to live as close to the line as possible, often attempting to get away with as much as we can without facing the consequences. This is a slippery slope, so what can we ask ourselves to step away from the edge?

  1. Do you have an example of a time you made a decision that was not wrong but unwise? How did it inform your following actions?
  2. Where do you currently invest most of your time? 
  3. How has culture shifted your personal boundary lines? Is there an area of your life that should be altered after asking yourself, “What is the wise thing to do?”
  4. What are you dreaming about, and what is one active step you can take today to get closer to accomplishing it?

NOTE: The following content is a raw transcript and has not been edited for grammar, punctuation, or word usage.

So when our kids were old enough to drive, I decided not to give them a curfew. You know, a curfew, a specific time to be home. And the reason is this. My personal experience with curfew as a teenage driver convinced me that the traditional approach to curfew is a terrible idea. At 16 years old, curfew transformed me into an overly aggressive weekend driver. Now on weekdays, I was fine, but on Friday and Saturday nights, not so much. And you know why? Because on Friday and Saturday nights, I found myself suffering from the five-minute syndrome. The five-minute syndrome. You know what this is? I can stay, well, I can stay just five more minutes. And then five minutes later, I can just stay five minutes. I’ve got five more minutes. And before long I had to be home in, you guessed it, actually, maybe you remember it, I had to be home in five minutes. I had to be home in five minutes, regardless of how many minutes it would actually take me to get home which explains my overly aggressive weekend driving. So when my kids started driving, I didn’t tell them what time to be home. I told them what time to leave for home and thanks to cell technology, I knew if they left on time.

Now, you have experienced some version of this curfew dynamic as an adult where your margin for error got gobbled up with just five more minutes thinking, whether it was one more drink, one more business trip, one more sleeve of cookies, one more pair of shoes, one more swipe of the credit card, whatever it is, the outcome is usually the same. And here’s where the math begins to fall apart. One more, one more rarely adds anything, when it comes to five-minute thinking, five more minute thinking, one more rarely adds anything. In fact worse, it usually subtracts. One more actually results in less oftentimes of what we value the most, right? And while it’s been a while since curfew dictated your driving habits, your current driving habits in fact are influenced by a similar dynamic unless you are a very unusual driver, you drive either at or slightly above the posted speed limit. And while most of us feel little to no guilt driving faster than the posted speed limit, none of us wanna get pulled over. So what do we do? Well, we choose the speed that we’re convinced allows us to break the law while avoiding an encounter with the law. And my point? Whether it’s curfew, diet, driving, spending, our natural inclination, you know this, our natural inclination is to live as close to the line as possible. Which line?

Well, the line between legal and illegal, the line between responsible and irresponsible, the line between moral and immoral, the line between ethical and unethical, the line between, “I’m still in control and I need help.” And it’s just human nature. It’s human nature to snuggle up to the edge of irresponsibility, disaster, embarrassment and to stay there as long as possible. It’s human nature to get by with as much as we can get by with, without becoming our own worst enemy, without being grounded, embarrassed or expelled, fired or kicked out of the house. And here’s the thing. Fueling, fueling this incessant flirtation with disaster is a flawed assumption that informs so many of our decisions. An assumption that, well, it basically impedes our ability to make good decisions. And this assumption is why I think we’re so comfortable living, dating, spending, eating, drinking, and driving on the edge of embarrassment or worse. And so for the sake of clarity, I’ll illustrate this assumption with four contrasting ideas. Here’s the assumption I’m talking about. If it’s not wrong, well, then it’s all right. If it’s not illegal, then clearly, it’s permissible. If it’s not immoral, it’s acceptable. And if it’s not over the line, it’s fine.

Now, if the problem with this way of thinking is not immediately apparent, just put on your older brother, sister hat for a moment. If you’re a parent, just put on your parent hat for a moment. I bet, and we’ve never met probably, but I bet you don’t set the bar that low for your children. You don’t set the bar that low for anybody that you care about. To embrace these assumptions is to organize your life or to organize somebody else’s life around the lowest common denominator, right? Essentially, we’re asking how low can I go? How close to bad can I get without actually being bad? How close to wrong can I get without actually doing something wrong? Or if you’re religious, how close to sin can I get without actually sinning? But it doesn’t stop there, does it? Before long we’re asking how far over the line can I go without getting caught or experiencing any consequences? How unethical, how immoral, how insensitive can I be without creating unmanageable outcomes? How long can I neglect my family or my finances or my health without feeling the effects? How much can I indulge an addictive behavior without actually becoming addicted? It’s a slippery, dangerous slope, and it all begins by asking the wrong question. Is there anything wrong with this? A question that usually leads to a second question, how did I get myself into this?

Drawing our lines, setting our limits, I’m establishing our moral or ethical standards on the borderline between right and wrong, legal, illegal, healthy and unhealthy, eliminates any margin for error. It is a foolish and it’s a dangerous way to live. And here’s the thing. I haven’t told you anything you don’t already know. We already know this, right? It’s why we respond the way we do when someone we love start snuggling up to one of those elusive lines. We don’t react to what they’re doing, do we? We react to where they’re heading. In those moments we just know intuitively that the issue isn’t, in fact, the question isn’t, is there anything wrong, illegal, or immoral about what they’re doing? We know intuitively that there’s a more important question, a better question that needs to be asked. A question that if we ask it, if they ask it, will ensure a better decision. A question that if asked and answered honestly and acted on will ensure that they avoid avoidable regret. And the truth is this, if you’ll get in the habit of asking this better question you’ll avoid avoidable regret as well. And that question, that question is the fourth of five questions we’re exploring in this series,Better Decisions, Fewer Regrets. Better Decisions, Fewer Regrets.

Now, if you’ve been tracking along with this, you know that the idea behind this series is the often-overlooked relationship between good questions and good decisions. Good questions actually set us up for better decisions. It could be argued that the decisions you make are no better than the questions that you ask. And I’m absolutely convinced that if you will ask and if you will answer honestly and if you will act on your answer to these five questions, you will make better decisions, and consequently, you will be forced to live with fewer regrets. Your life will be better, and the people who look to you, the people who depend on you, their lives will be better as well. Because we aren’t the only people impacted by our decisions. Are we? And we aren’t the only people impacted by our regrets either. Again, if you’ve been following along in this series, you’ll know that the first question we explored is called the integrity question. The integrity question, and the integrity question is, “Am I being honest with myself? Am I being honest with myself really?” The easiest person to deceive in your life, is the person you see every morning in the mirror. And as long as you are lying to yourself, you will never get to where you wanna be because you’ll never get to where you wanna be until you’re honest about where you currently are.

Our second question is the legacy question. The legacy question is, “What story do I wanna tell? What story do I wanna tell?” When the decision you’re in the process of making right now, whether it’s relational, financial, academic, professional whatever it is, when the decision that you’re making right now, is nothing more than a story you tell. What story do you wanna tell? And the good news is, you get to decide, but you decide the story of your life one decision at a time. Because as far as it’s up to you, you write the story of your life one decision at a time.

Now, last time we were together, we explored the conscience question. The third question is the conscience question. The conscience question is, “Is there a tension that deserves my attention?” When everything looks good on paper, when everybody’s nodding in agreement, but there’s something on the inside that just doesn’t feel right about an option that you’re considering, you can’t put your finger on it, but there’s just something not right, pause and pay attention to that tension.

And that brings us at last to our fourth question. And I call this one the maturity question. The maturity question. Now, the reason I call it the maturity question and I hope this is a personal challenge. I call it the maturity question because asking this question requires and is evidence of, I think maturity. And refusing to ask this question, well, it takes us back to the statement we began this series with from Proverbs, the one I suggested you memorize, “The prudent see danger.” You remember this? “The prudent see danger and they take refuge.” Prudent people are wise people. They embrace the reality that one thing leads to another and they decide their lives accordingly. The unwise, the immature, the naïve, you know how this statement goes, “The prudent see danger and take refuge, but the simple, the simple, they keep going.” And what happens? They pay the penalty.

So our maturity question is, the maturity question is, what is the wise thing to do? What is the wise thing to do. When making a decision of any consequence, I want you to pause and ask, “Okay, what is the wise thing for me to do?” The option you’re considering maybe legal, maybe acceptable, permissible, and industry-standard, not exactly immoral, but is it wise? Now, here’s something mature people understand. This is why I love calling this the maturity question. Here’s something that mature people understand and recognize and accept as fact. A decision, don’t miss this, a decision can be both not wrong and unwise at the same time. A decision or an option you’re exploring can be not wrong, it’s not wrong, but it can be not wrong and unwise at the same time.

Let me explain this. Isn’t it true, and I hate to bring this up, but isn’t it true that your greatest regret, and when I say greatest regret I’m talking about that moment of regret, the moment that you would give almost anything to be able to go back and relive or undo, the decision you would like to be able to go back and unmake. The tipping point, the point of no return. That moment, that moment. Isn’t it true that your greatest regret was preceded by a series of unwise decisions? They weren’t wrong. They weren’t illegal. They weren’t necessarily immoral, but looking back, they were terribly, terribly unwise. And that series of unwise decisions paved the way, think about it, paved the way to the moment in time, you’ve regretted ever since.

So, to avoid five more minutes syndrome, to create moral and ethical and financial margin, ask of every invitation, every opportunity, every option that comes your way, what is the wise thing for me to do? What is the wise thing for me to do? Now, the Apostle Paul, spells this out for us in the letter that he wrote to Christians living in Ephesus. We call it the Book of Ephesians and here’s what he writes. And he goes right to the heart of this tension that all of us live with and really that all of us wrestle with every single day.

Here’s what he writes, he says, “Be very careful then how you live.” Be very careful then how you live. “Not as unwise.” Here’s our word, “Not as unwise, but as wise. Making the most of every opportunity because the days are evil.” So while a lot has improved since the 1st century, apparently human nature has not. Ancient folks and us modern folks are equally prone to live carelessly and unwisely, to snuggle up to the edge of disaster, and pretty much stay there as long as possible. And the Apostle Paul comes along and he says, “Stop it. I want you to be careful how you live. Don’t be careless.” This is the grid through which we are to evaluate every invitation, every opportunity that comes our way, financial, relational, professional, academic, whatever it might be.

And thus our question, what is the wise thing to do? Paul continues with a bit more explanation. He says “Making the most, making the most of every opportunity.” Literally in the Greek, this phrase could be translated, literally, redeeming or ransoming the time. Redeeming or ransoming the time. This is where the English word, opportunity comes from. Don’t you wish, think, about this, don’t you wish you could go back and reclaim or redeem all the time you wasted on bad decisions? Along with all the time you had to spend making up for those bad decisions? I do.

And for you, that may be just a few weeks or weekends scattered around your past, but it might be an entire season of your life. Either way, imagine, imagine having the opportunity to relive or re-spend or reallocate those days, weeks, or even years, not to mention the money. I mean, what if you had an opportunity to go back and invest that time in more productive, healthy life-giving activities. Imagine where you’d be today? And I know this is hard, as painful as it is to think back and to look back, it’s necessary in order to appreciate the invitation embedded in the Apostle Paul’s words, because here’s what he’s doing. Paul is inviting you. Paul is inviting us to invest our time wisely from this moment forward, from this day forward. You are invited to make the most of or to redeem or to leverage your most valuable asset, your time. To invest your time in a way that actually propels you forward toward a preferred future.

But he’s not through. Then he tacks on this kind of odd warning. He writes this, “Making the most of every opportunity because the days are evil.” Evil days, what’s he talking about? Well, you know this, we don’t live in a morally ethically neutral culture, do we? I mean, think about it. When is the last time, when is the last time you heard or saw, or even read an ad that encouraged you to be careful, to be wise, to be self-controlled? I’m guessing maybe never. I mean, has a sales associate ever suggested you go home and think it over before making a purchase? Probably not. Which means, and this is Paul’s point, this is on us. We aren’t gonna get much help from culture. The friends around us, maybe, but not culture. The gravitational pull of culture is what? It’s now, not later. It’s more, not less. This is why our fourth question, practically speaking, may in fact be the best question ever. It’s why I call it the maturity question.

So, in an attempt to anchor your conscience to our fourth question, I wanna suggest that you ask this question from three perspectives: Your past, your present, and your future. In fact, this is the version I taught my children when they were growing up, and this is the version of the question I’ve taught some of you before. In light of my past experience, my current circumstances, and my future hopes and dreams, what is the wise thing for me to do? In light of my past experience, my current circumstances, my future hopes and dreams, what is the wise thing for me to do? Now, I imagine you’re familiar with little quip that says, “Those who can’t remember the past are condemned or are doomed to repeat it.” You’ve heard that before. Well, on a personal level, it could be restated this way. Those who don’t pay attention to what got them into trouble yesterday are liable to wind up in the same trouble tomorrow. Not as catchy, but you get the point.

The point being this, our past, our personal past, predisposes us to specific temptations, addictions, blind spots, just to name a few, right? Temptations, addictions, and blind spots that may not be temptations, addictions, or blind spots to anybody else. So in light of your past experience, in light of your personal past experience, what is the wise thing for you to do? Every decision, every decision, every invitation, every opportunity that comes your way needs to be filtered through that question. I have a friend, I’ll call him Steve and Steve receives really unsettling advice about halfway through his premarital counseling with his soon to be wife, Shauna. The counselor said to Steve, “Steve, in light of your family history, when you and Shauna return from your honeymoon, you need to come back and see me alone.” [chuckle] And then it got worse. The counselor said, “I want to introduce you to another counselor who specializes in family systems.” Now like most men, I mean, I can identify with this, you know, Steve felt like he’d already gone the extra mile by attending and paying for four premarital sessions with his counselor, and now this. And Steve’s next question was the question I think most of us would have asked, “How long is that gonna take?”

His counselor smiled. He told me this story, his counselor smiled and said, “Well, probably several months.” Of course, Steve is stunned, he was shocked. Actually, he said, “He got mad.” And here’s the quote I love. He said, “I got so mad, I pretty much confirmed my need for more counseling.” And their counselor recognized that Steve and Shauna were not gonna be grappling with typical first-year marriage problems. They were about to hit the buzzsaw of Steve’s preexisting condition, his past. Now, fortunately, Steve did what very few men in my experience are willing to do. Two weeks after the honeymoon, he’s back in the counselor’s office alone. Why? Well, in light of Steve’s past experience, it was the wise thing for him to do. Think about it. It wouldn’t have been wrong not to go back. It wouldn’t have been illegal or immoral not to go back, but Steve would tell you it certainly would have been unwise. That was years ago. He’s convinced, he’s convinced that that second round of counseling saved his marriage. His words, “I would have blown it up and blamed her.”

So what about you. In light of your past experience, what is the wise thing for you to do? Financially, professionally, academically, where are you set up to fail because of something in your past, perhaps something you had no control over in light of your personal past experience, what is the wise thing? Not to get by thing, not the what everybody else is doing thing, what is the wise thing for you to do? In light of my past experience and then my current circumstances, my current circumstances, now you know this, life is seasonal, right? So you owe it to yourself and the people around you to take your current, your current emotions, your current state of mind into account whenever you’re making a decision. Most of my apologies, most of my apologies stem from my propensity to react in the moment to the moment. When I wait, my responses are better, when I wait, my responses are more polite, when I wait, my responses are more accurate, when I’m mad, when I’m mad, the wise thing for me to do is nothing.

So when asking our fourth question, we would do well to take into account what’s going on right now in light of your current circumstances, in light of your current state of mind, what’s the wise thing for you to do? Did you just get out of a relationship? Would it be wrong to jump back into another one? No, but in light of your recent circumstances and the emotions trailing along behind, is it the wise thing for you to do? Remember, our greatest regrets, and I’m talking about usually our greatest relational regrets, our greatest regrets are almost always preceded by a series of unwise decisions. Jumping back into the dating game on the heels of a divorce or a break-up is usually a gateway decision, it leads to regret. In light of your current circumstances, what is the wise thing for you to do?

And that brings us to our third and final perspective. In light of my past experiences, my current circumstances and my future hopes and dreams, what is the wise thing for me to do? What is the wise thing for you to do.Now, from time to time, if you tune in or if you’re a part of one of our churches, I’ll ask you, What breaks your heart? What breaks your heart? And I’ll tell you what breaks my heart, it’s related to the third facet of this question.

What breaks my heart is watching people make decisions that undermine their own future, their own future hopes and dreams. It breaks my heart to watch individuals or couples make relationship decisions that are gonna undermine their relationship. It breaks my heart to watch teenagers make decisions that are gonna result in consequences that trail around behind them for maybe a decade or even two. It breaks my heart to watch parents parent in a way that will eventually drive a wedge between them and their children. It breaks my heart to watch people engineer their own unhappiness, perhaps that’s why I’m convinced this third application to our fourth question is the most important application in light of your future hopes and dreams. In light of your future hopes and dreams, what is the wise thing for you to do?

Chances are, you have some idea of what you want your future to look like, right? I mean you have a mental picture of a preferred future, what it could be and what it should be. You may have gone to the trouble of writing it down, you may not have a plan of how to get there, but you have some sense of where you wanna be, right? And I’m guessing, I’m guessing that when you envision your future, you don’t envision yourself alone because nobody does, but here’s the challenge, here’s the challenge, when it comes to dreams, when it comes to your dream, the deck is stacked against you because life is hard on dreams, there’s always a headwind, and that being the case, if we’re not careful, if you’re not careful, you have the potential to contribute to the demise of what you hope for.

And here’s the thing, I don’t want you to rob yourself of your own future. Nobody plans to undermine their own future, they just don’t plan not to. But asking the wisdom question and acting on the wisdom question, that’s how you plan, not to. In light of your future hopes and dreams, what is the wise thing for you to do? Asking this question with the future in mind brings… Well, it brings clarity to whatever option you’re considering, it serves as a… Like a purifying light, all the deceptive shades of grey, they almost immediately dissipate our best option, or our best options become… Well, they become clear.

Painfully clear in fact, they become so clear, we’re tempted to look away to excuse ourselves away, but I’m not hurting anybody, I can handle it. There’s no law against it, God will forgive me. And here’s the thing, our excuses… Our excuses are persuasive because they’re mostly true. You aren’t doing anything wrong, yet, you can handle it, initially, it isn’t illegal, God will forgive you. So what? That’s all beside the point, right? The purpose of this fourth question isn’t to stop you from doing something wrong, it’s to keep you from doing something unwise. Again, unwise is a gateway, it’s the gateway to regret, it paves the way to that tipping point, the point… In some cases, the point of no return, so would you be willing…

Here’s the challenge, would you be willing to put away your old worn out excuses once and for all? Come on, they have never served you well, they just silence your conscience, they cloud your reasoning, and ultimately they really just diminish your ability to hear the voices of wisdom, around you. Our excuses, you know what they do? They escort us to the threshold of regret, and once they get us there, do you know what your excuses do? They abandon you there with no margin for error. You’ve been there.

I don’t want you to ever go there again, so just decide to be done with all that. Instead of excusing yourself forward, dream and plan your way forward. Ask, in light of my future hopes and dreams, what is the wise thing for me to do? In light of where you wanna be financially, five or 10 years from now, what’s the wise thing to do now? I mean, you’re gonna be somewhere five or 10 years from now financially, right? Shouldn’t you decide? Do you know what, if you don’t decide, you know who will decide? Retailers and lenders who care nothing about you, they will decide for you. And what’s true financially is true relationally, academically, professionally as well.

So come on, where do you wanna be? Decide, write it down. If you’re single, come on, if you’re single in light of what you ultimately want relationally, even romantically? What’s the wisest way to content your relationships right now. What are you doing now? Think about it, what are you doing now that has the potential to rob you of your preferred future relationally? Now, that’s a hard question to answer, honestly, which takes us back to our first question in this series, really, are you being honest with yourself? Are you being honest with yourself really? Are your relationships… Come on, are your current relationships paving the way to your preferred relational future, or are they escorting you to a place you don’t wanna be? A place you swore you would never go. In light of what you want later, what is the wise thing to do right now?

If you’re married and you’re planning to go the distance with your spouse to finish together to maybe enjoy grandchildren together, what can you do right now to facilitate that dream? What or who puts that dream at risk? What is the wise thing to do as it relates to protecting your marriage? You have children? Come on, what do you envision for your children in the future? What do you envision in terms of your relationship with your children in the future? What’s the wise thing to do right now to protect that dream?

Here’s the thing, you know this, everybody ends up somewhere in life, right? I want you to decide to live and to end up somewhere on purpose, and wisdom paves the way. Now, when teaching this question to university students or high school students, I always encourage them to commit the following little rhyme to memory. It goes like this, I wrote this many, many years ago, there’s good and there’s bad, but that’s not my cue, but rather what is the wise thing to do. There’s good and there’s bad, but that’s not my cue. In other words, good and bad, that’s no longer the filter through which I’m making decisions, my filter is better than that.

There’s good and there’s bad, but that’s not my cue, but rather, what is the wise thing to do? Don’t settle for good, don’t settle for legal, permissible, acceptable or even tolerable, if you do, you’ll eventually find yourself living dangerously close to regret. You’re better than that. You deserve better than that. Your family, the people who depend on you, they deserve better than that. Think about this, you are a unique blend, you are a unique blend of past experiences, current circumstances, and future hopes and dreams, and this question, the wisdom question allows you to customize the decision-making process to your specific professional financial, relational or academic aspirations, so ask it. Ask it even if you don’t plan to act on it. What is the wise thing for me to do? You owe it to yourself to know… I think you owe it to the people depending on you to know as well. So one last time. In light of your past experience, your current circumstances and your future hopes and dreams, what is the wise thing for you to do? And we’ll pick it up right there next time as we explore our fifth and final question, the relationship question.

Now, before you go, of course, three questions to keep this conversation going or to get a conversation started, question number one, question number one, does this statement ring true for you? Our excuses escort us to the threshold of regret and abandon us there with little margin for error. I want you to just talk about that statement, does that ring true for you? Can you think of an example that you might even be willing to share with the people you’re watching with? Number two, when making the decision, why are we or why are you more prone to evaluate options through the filters of legal, moral, ethical and acceptable than through the filter of wisdom. Again, that thing I talked about today is even probably new for you, we know this, but why are we so prone to ignore wisdom and to go through these other filters. Number three, would you commit to asking… Not acting on, okay, that’s later maybe, but would you at least commit to asking the wisdom question for the next seven days, every time you make a decision?

You don’t have to act on it but would you be willing to commit to asking the wisdom question, what is the wise thing for me to do for the next seven days every single time you make any major decision? Now, I’m passionate about this because I was raised on this question, in fact, I raised my kids on this question, as many of you know, this question actually permeates our children and students curriculum at all of our churches. We wanna raise a generation of students who walk wisely because the days are evil, but come on, the best way to ensure that the next generation gets this right is for them to see this generation get this right. So let’s walk wisely. If we do, we will make better decisions and we will certainly be left with fewer regrets. I’d love to pray for us.

Heavenly Father, it’s so simple. Nobody is arguing with this, we’ve been on both sides, we’ve benefited from being wise, we’ve paid the price for being foolish, so give us the courage to ask this question. I pray, Father, for everyone listening or watching, that this week, for the next seven days, you would bring this question to mind, and that this would become a habit for life. What is the wise thing for me to do? And I pray all of this in the matchless name of Jesus. Amen.